Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl}indoline-2,3-dione.

ABSTRACT: The title compound, C₁₄H₁₅BrClNO₄, consists of a 5-bromo-indoline-2,3-dione unit linked to a 1-{2-[2-(2-chloro-eth-oxy)eth-oxy]eth-yl} moiety. In the crystal, a series of C-H?O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R ₂ ²(8), R ₂ ²(12), R ₂ ²(18) and R ₂ ²(22) ring motifs. ?-? contacts between the five-membered dione rings may further stabilize the structure, with a centroid-centroid distance of 3.899?(2)?Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H?H (28.1%), H?O/O?H (23.5%), H?Br/Br?H (13.8%), H?Cl/Cl?H (13.0%) and H?C/C?H (10.2%) inter-actions. Hydrogen bonding and van der Waals inter-actions are the dominant inter-actions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap. The chloro-eth-oxy-ethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665?(8):0.335?(6).

SUBMITTER: Abdellaoui O 

PROVIDER: S-EPMC6727053 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature